2026-06-09

2026-06-09 Tuesday - Some Considerations When Evaluating The Benefits/Risks of Establishing a New Client Relationship

[image source: geralt on pixabay dot com]
 

This post summarizes some thoughts I wanted to share, in response to this LinkedIn post (asking for input), by Jurgen Appelo


When I evaluate the benefits/risks of establishing a new client relationship, here are just some of the factors I consider:

⏹️ Duration of the specific engagement's SOW under discussion.

⏹️ Potential duration of the longer-term relationship, and follow-on SOWs.

⏹️ Fee size, payment structure, and invoicing/payment terms.

⏹️ Financial viability of the client, and risks of their default.

⏹️ Any external information / evidence of toxicity levels within their culture.

⏹️ Degree of bureaucracy burdens (e.g., their strategic sourcing / vendor management processes, contract negotiations, reporting, billing, legal, compliance, security, insurance, etc.).

⏹️ Long-term value of the client relationship, itself.

⏹️ Long-term value of the relationships established, during the engagement.

⏹️ Potential future value of client recommendations, business referrals.

⏹️ Reputation of the client, and any risks associated therein.

⏹️ Client's adherence to ethical business practices, or lack thereof.

⏹️ Client's legal exposure risks (previous history, current, pending).

⏹️ Client's regulatory compliance risks (previous history, current, pending).

⏹️ Potential blast-radius if things go sideways (re: events outside of my control).

⏹️ Contractual terms that impose egregious burdens, and that may potentially exceed the total value of the engagement compensation.

⏹️ Intangible value components (e.g., potential for learning & personal growth: acquisition of new skills, working with new technologies, new concepts, best practices, new/increased industry domain knowledge, etc.).

⏹️ Potential for negotiating retention of some/all of the intellectual property I will create during the engagement.

⏹️ Contractual clauses that make broad claims on intellectual property I possessed before the engagement, or created outside of the scope of contract - during the engagement, or created after the engagement ends). 

⏹️ Travel requirements (difficulty, frequency, costs, and reimbursement considerations).

⏹️ Personal safety considerations (location of their offices; crime rates in the area; travel to areas that are active war zones, or high potential for terrorist attacks; degree of difficulty to effect escape/evasion if there is a risk of a coup d'état, or regime collapse). [1]

⏹️ The "Fun Quotient" of working with the team within the organization. 

⏹️ {Novelty | Difficulty | Challenge} factor (harder problems = higher score = more attractive)

⏹️ Bragging Rights - for a successful completion of the engagement.

 

(these are drawn from over the decades of my career, in different roles, in different organizations, and  performed within the scope of my own consulting practices) 

Years in Professional Services Consulting: 30+ 

Largest Successful Proposal Pitched: $80M 

Shortest successful client "Close The Deal" meeting: 7 minutes. 

Shortest International Assignment Location: Hong Kong 

Shortest contract document:  1-page. 

Longest contract negotiation: multiple months 

Best contract outcome:  Initial 3-month SOW, extended (continuously), over 4 years. 

Geographic Scope: Global 

Favorite International Assignment: Sydney Australia 

Most Unexpected Delight: Istanbul, Turkey

Worst Food Poisoning Experience: Istanbul, Turkey (during a cholera outbreak) 

Most Unusual Assignment Location:  Wall Street, New York, NY (living in the Marriott, at the former World Trade Center Towers)

Most Unusual Layover Experience:  Singapore, SilverKris Lounge (ask me about that sometime, over a drink)

Most Unusual Luggage Disaster: Tahiti, my luggage was left on the tarmac - took a week to catch-up with me in Sydney.

Best Meal, In All My Travels: A small Italian restaurant, in a narrow alley, London

Best Expat Community Experience: Warsaw Poland 

 

[1] While many reading this may dismiss this entry's importance – I can assure you that it is based on lessons-learned – of personal experiences, actual bullets dodged, and attacks narrowly avoided.

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